Biomimetic Total Synthesis and Investigation of the Non-Enzymatic Chemistry of Oxazinin A

4Citations
Citations of this article
8Readers
Mendeley users who have this article in their library.

This article is free to access.

Abstract

We report the first total synthesis of an antimycobacterial natural product oxazinin A that takes advantage of a multi-component cascade reaction of anthranilic acid and a precursor polyketide containing an aldehyde. The route utilized for the synthesis of the pseudodimeric oxazinin A validates a previously proposed biosynthetic mechanism, invoking a non-enzymatic pathway to the complex molecule. We found a 76 : 10 : 9 : 5 ratio of oxazinin diastereomers from the synthetic cascade, which is an identical match to that found in the fermentation media from the fungus Eurotiomycetes 110162. Further investigation of the non-enzymatic formation of oxazinin A using 1H-15N HMBC NMR spectroscopy allowed for a plausible determination of the stepwise mechanism. The developed route is highly amenable for the synthesis of diverse sets of analogs around the oxazinin scaffold to study structure–activity relationships (SAR).

Cite

CITATION STYLE

APA

Aniebok, V., Shingare, R. D., Wei-Lee, H., Johnstone, T. C., & MacMillan, J. B. (2022). Biomimetic Total Synthesis and Investigation of the Non-Enzymatic Chemistry of Oxazinin A. Angewandte Chemie - International Edition, 61(38). https://doi.org/10.1002/anie.202208029

Register to see more suggestions

Mendeley helps you to discover research relevant for your work.

Already have an account?

Save time finding and organizing research with Mendeley

Sign up for free